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Search results; Over 1,000 homes in Old Saybrook

Guest favourite
Cottage in Old Saybrook
Luxury Driftwood Cottage @ Saybrook Point
3 bedrooms, 3 beds, 2 private bathrooms
7–13 Sept
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4.9 out of 5 average rating, 67 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.75 out of 5 average rating, 254 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 23 reviews
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
27 Aug – 1 Sept
New place to stay
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 100 reviews
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Home in Old Lyme
Waterfront! The Perfect Cozy Cottage in Old Lyme
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 110 reviews
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 165 reviews
Top guest favourite
Room in Madison
Madison Cozy Studio with Private Entrance
3 beds, 1 bathroom
11–16 Aug
4.87 out of 5 average rating, 597 reviews
Guest favourite
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
2 bedrooms, 3 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.91 out of 5 average rating, 139 reviews
Guest favourite
Bungalow in Westbrook
Adorable single story cottage-by-the-sea
2 bedrooms, 2 queen beds, WC
15–20 Sept
4.87 out of 5 average rating, 54 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
13–18 Oct
4.94 out of 5 average rating, 172 reviews
Top guest favourite
Tiny home in East Lyme
Couple’s Lakefront Cabin | Tiny House with a View
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 142 reviews